Process for preparing halogenated pyridine derivatives

ABSTRACT

The present invention relates to a process for preparing halogenated pyridine derivatives of the formula (II) proceeding from compounds of the structure Q-H via intermediates of the formula (IIIa) or (IIIb) 
                         
in which
     Q is a structural element   

                         
where the symbol # indicates the bond to the rest of the molecule and A, Q 1 , Q 2 , Q 3 , Q 4 , Q 5  and Q 6  have the definitions given in the description,
     W is halogen,   Y is halogen, CO 2 R 1  or NO 2 , where R 1  is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl, and   R 2  is halogen or —O-pivaloyl.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage entry of International ApplicationNo. PCT/EP2017/070184, filed Aug. 9, 2017, which claims priority toEuropean Patent Application No. 16184368.5, filed Aug. 16, 2016.

BACKGROUND Field

The present invention relates to a process for preparing halogenatedpyridine derivatives of the formula (II)

proceeding from compounds Q-H via intermediates of the formula (IIIa) or(IIIb)

in which the structural elements shown in the formulae (II), (IIIa) and(IIIb) have the definitions given below. The invention further relatesto halogenated pyridine derivatives and intermediates of this kind.

Description of Related Art

Halogenated pyridines derivatives of the formula (II) are of greatindustrial significance for the pharmaceutical and agrochemical industryand are an important intermediate, inter alia, in the preparation ofcompounds that are effective as pesticides, for example.

The literature discloses that compounds of the formula (II) can beprepared, for example, in a first step by condensation ofpyridine-2-carboxylic acid derivatives with ortho-substitutedbis(amine), amine alcohol or amine thiol (hetero)aryl derivatives in thepresence of a condensing agent (cf. US2003/69257 or WO2006/65703) andthen, in a second step, by further condensation as described inWO2012/86848. However, the chemical synthesis methods that have beendescribed in the prior art to date for such halogenated pyridinederivatives very frequently make use of methods that are noteconomically implementable from an industrial point of view and/or haveother disadvantages.

Disadvantages are low chemical yields, performance at very hightemperatures (about 150 to 250° C.) and the possibility of difficultregio- and chemoselectivity of the condensation, especially in the caseof imidazopyridine and imidazopyridazine derivatives. The preparation istherefore very expensive and unsuitable for industrial scale commercialprocesses. Moreover, corresponding compounds are barely commerciallyavailable. This is especially true of 3,6-dihalopyridine-2-carboxylicacid derivatives.

With regard to the disadvantages outlined above, there is an urgent needfor a simplified, industrially and economically performable process forpreparing halogenated pyridine derivatives, especially halogenatedpyridine derivatives of the formula (II). The halogenated pyridinederivatives obtainable by this process sought are preferably to beobtained with good yield, high purity and in an economic manner.

SUMMARY

It has been found that, surprisingly, halogenated pyridine derivativesof the formula (II) can be prepared advantageously in a process using anorganozinc base.

The present invention accordingly provides a process for preparingcompounds of formula (II)

in which (configuration 1)Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon,        W is halogen, and        Y is halogen, CO₂R¹ or NO₂, where R¹ is (C₁-C₆)-alkyl or        (C₁-C₆)-haloalkyl,        characterized in that, in a first process step a), a compound        Q-H in which Q is as defined above        is reacted with an organozinc base of the structure        (NR³R⁴)—Zn—R² or (NR³R⁴)₂—Zn in which        R² is halogen or —O-pivaloyl and        R³ and R⁴ together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂—        group, where each of these groups may optionally be substituted        by 1, 2, 3 or 4 R⁵ radicals and R⁵ is selected from the group        consisting of methyl, ethyl, n-propyl and i-propyl,        to give a compound of the formula (IIIa) or the formula (IIIb)

in which Q and R² each have the definitions given above,and this compound of the formula (IIIa) or (IIIb) is reacted in a secondprocess step b) with a compound of the formula (I)

in which X is halogen and W and Y each have the definitions given above,in the presence of a catalyst, to give the compound of the formula (II).

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Preferably, Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ represent not more than fivenitrogen atoms overall and further preferably not more than fournitrogen atoms overall.

Preferred and particularly preferred definitions of the Q, W, R¹, R², Xand Y radicals included in the aforementioned formulae (I), (II), (IIIa)and (IIIb) of the process of the invention are elucidated hereinafter,with more specific description of the organozinc base further down, andso the preferred configurations of the base are specified at that point.

(Configuration 2)

Q is preferably a structural element from the group of Q1 to Q15

-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl,-   W is preferably fluorine, chlorine or bromine,-   R² is preferably halogen, especially chlorine, bromine or iodine,-   X is preferably halogen, especially bromine or iodine, and-   Y is preferably fluorine, chlorine, bromine, CO₂R¹ or NO₂, where R¹    is (C₁-C₄)-alkyl.    (Configuration 3)-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl,-   W is more preferably fluorine or chlorine, especially fluorine,-   R² is more preferably chlorine,-   X is more preferably bromine or iodine, especially iodine, and-   Y is more preferably chlorine, bromine, CO₂R¹ or NO₂, where R¹ is    (C₁-C₄)-alkyl.    (Configuration 4)-   Q is most preferably the structural element Q3 or Q14,-   R⁷ is most preferably methyl, ethyl, n-propyl or isopropyl,    especially methyl,-   A is most preferably trifluoromethyl,-   W is most preferably fluorine,-   R² is most preferably chlorine,-   X is most preferably iodine, and-   Y is most preferably chlorine, bromine, CO₂R¹ or NO₂, where R¹ is    methyl.

The radical definitions and elucidations given above apply both to theend products and intermediates and to the starting materials in acorresponding manner. These radical definitions can be combined with oneanother as desired, i.e. including combinations between the respectiveranges of preference.

Preference is given in accordance with the invention to those compoundsin which there is a combination of the definitions listed above as beingpreferred.

Particular preference is given in accordance with the invention to thosecompounds in which there is a combination of the definitions listedabove as being more preferred.

Very particular preference is given in accordance with the invention tothose compounds in which there is a combination of the definitionslisted above as being most preferred.

In a further preferred embodiment of the invention, Q is Q1 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 5).

In a further preferred embodiment of the invention, Q is Q2 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 6).

In a further preferred embodiment of the invention, Q is Q3 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 7).

In a further preferred embodiment of the invention, Q is Q4 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 8).

In a further preferred embodiment of the invention, Q is Q5 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 9).

In a further preferred embodiment of the invention, Q is Q6 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 10).

In a further preferred embodiment of the invention, Q is Q7 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 11).

In a further preferred embodiment of the invention, Q is Q8 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 12).

In a further preferred embodiment of the invention, Q is Q9 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 13).

In a further preferred embodiment of the invention, Q is Q10 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 14).

In a further preferred embodiment of the invention, Q is Q11 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 15).

In a further preferred embodiment of the invention, Q is Q12 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 16).

In a further preferred embodiment of the invention, Q is Q13 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 17).

In a further preferred embodiment of the invention, Q is Q14 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 18).

In a further preferred embodiment of the invention, Q is Q15 and R⁷, A,W, R², X, and Y have the definitions given in configuration 1 or thosegiven in configuration 2 or those given in configuration 3 or thosegiven in configuration 4 (configuration 19).

Advantageously, the halogenated pyridine derivatives of the formula (II)can be prepared by the process according to the invention with goodyields and in high purity. A great advantage of the process according tothe invention is the regioselectivity thereof. Because of the very goodfunctional group tolerance of zinc reagents, zinc bases are veryattractive. Especially advantageous is the possibility of being able toconduct Negishi couplings even at distinctly lower temperatures, inwhich case even functional groups that are sensitive at highertemperatures, such as esters or fluorine atoms, are tolerated inprocesses according to the invention without impairing theregioselectivity that exists. Moreover, Negishi cross-couplings withinthe context of a process according to the invention can also give riseto good yields of target product in the presence of ortho substituentson the pyridine skeleton, even though such couplings with 2-substitutedpyridine derivatives have to date been known for giving low yields.Thus, further and/or more flexible derivatizations of reactant andproduct are possible without having to constantly alter or adaptsynthesis routes.

The process according to the invention can be elucidated by thefollowing scheme (I):

In this scheme, Q, W, R², X, and Y and, within the respectivedefinitions, any further structural elements present each have thedefinitions given above. The compounds shown in brackets are theintermediate (formula IIIa or formula IIIb) which are reacted furtherwith a compound of the formula (I) to give the compound of the formula(II). Accordingly, the process according to the invention can be dividedinto the two process steps a) and b), step a) being the conversion ofthe compound Q-H to the respective intermediate and step b) being thefurther conversion of the intermediate to the compound of the formula(II).

General Definitions

In the context of the present invention, the term halogen (Hal), unlessdefined otherwise, encompasses those elements selected from the groupconsisting of fluorine, chlorine, bromine and iodine.

The term “halides” in connection with the present invention describescompounds between halogens and elements of other groups of the PeriodicTable, which can give rise to halide salts (ionic compounds (salts)which consist of anions and cations because of the great difference inelectronegativity between the elements involved and are held together byelectrostatic interactions) or covalent halides (covalent compoundswhere the difference in electronegativity is not as great as in theaforementioned ionic compounds, but the bonds have charge polarity),depending on the nature of the chemical bond. Particular preference isgiven in accordance with the invention to halide salts.

The term “pivaloyl” in the context of the present invention describesthe deprotonated radical of pivalic acid (X) having the empiricalformula (CH₃)₃CCO₂H.

“O-pivaloyl” correspondingly means that the bond of the pivaloyl radicalis via the deprotonated oxygen atom of the acid group.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. Among these, preference is given toC₃-C₆-alkynyl radicals and particular preference to C₃-C₄-alkynylradicals. The alkynyl radical may also contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Unless defined differently, halogen here is fluorine,chlorine, bromine or iodine, especially fluorine, chlorine or bromine.Alkyl groups substituted by one or more halogen atoms are (-Hal), forexample, selected from trifluoromethyl (CF₃), difluoromethyl (CHF₂),CF₃CH₂, ClCH₂ or CF₃CCl₂.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

The synthesis of compounds Q-H as reactants of a process according tothe invention is known in principle to those skilled in the art. Forexample, compounds Q-H with Q=Q1, Q2, Q3, Q14 or Q15 can be obtainedfrom corresponding pyridinediamine derivatives by ring closure to givethe respective azole compound, as described, for example, inWO2014/100065 or WO2015/017610 preferably under acidic conditions.Alternative syntheses are likewise possible, but are more complex and asa result generally less economically advantageous.

The conversion of the compounds Q-H to compounds of the formula (IIIa)or (IIIb) in the first process step (step a)) is effected in thepresence of an organozinc base of the structure (NR³R⁴)—Zn—R² or(NR³R⁴)₂—Zn, in which (configuration B-1)

R² is as defined above (configuration 1) (and is therefore halogen or—O-pivaloyl),

R³ and R⁴ together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂— group,where each of these groups may optionally be substituted by 1, 2, 3 or 4R⁵ radicals and

R⁵ is selected from the group consisting of methyl, ethyl, n-propyl andi-propyl.

It is preferable that (configuration B-2)

R² is as defined above as preferred (configuration 2) (and is thereforehalogen, especially chlorine, bromine or iodine),

R³ and R⁴ together form a —(CH₂)₅— group, where each of these groups mayoptionally be substituted by 1, 2, 3 or 4 R⁵ radicals and

R⁵ is selected from the group consisting of methyl and ethyl.

It is particularly preferable that (configuration B-3)

R² is as defined above as more preferred (configuration 3) or as mostpreferred (configuration 4) (and is therefore chlorine) and

R³ and R⁴ together form a —(CH₂)₅— group substituted by 4 methyl groups.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective ranges ofpreference.

In a very particularly preferred configuration of the base according tothe invention, the structural element (NR³R⁴) is tetramethylpiperidine(TMP) of formula (IV).

Organozinc bases most preferred in accordance with the invention areaccordingly characterized in that zinc is bound by TMP, especially inthe form of zinc halide and most preferably in the form of zincchloride. Bases of this kind have the following structure of the formula(V) (configuration B-4)(TMP)_(x)ZnCl_(2-x)  (V)in which x is the number 1 or 2. Among these, preference is given inturn to bases with x=1 (configuration B-5) of formula (VI):

In a further preferred embodiment of the process according to theinvention, the organozinc base is present in conjunction with alkalimetal or alkaline earth metal halides. This is especially true of basesof the formulae (V) and (VI). Particularly preferred alkali metal oralkaline earth metal halides of this kind are lithium chloride andmagnesium chloride, very particular preference being given to lithiumchloride. Organozinc bases that are very particularly preferred inaccordance with the invention are accordingly TMP ZnCl.LiCl or (TMP)₂Zn.2LiCl (configuration B-6). Most preferred is TMP ZnCl.LiCl (VII;configuration B-7).

Specific combinations of compounds of the formulae (I), (II) and (IIIa)or (IIIb) with bases according to the invention are cited hereinafter byway of example in Table 1, these being employable in a process accordingto the invention. Since, in some configurations, the structural elementR² is present both in the base according to the invention and in thecompound of the formula (IIIa), the narrowest definition applies to R²in each case.

TABLE 1 Compounds of the formulae (I), (II) and Number (IIIa) or (IIIb)Base according to 1 Configuration 1 Configuration B-1 2 Configuration 1Configuration B-2 3 Configuration 1 Configuration B-3 4 Configuration 1Configuration B-4 5 Configuration 1 Configuration B-5 6 Configuration 1Configuration B-6 7 Configuration 1 Configuration B-7 8 Configuration 2Configuration B-1 9 Configuration 2 Configuration B-2 10 Configuration 2Configuration B-3 11 Configuration 2 Configuration B-4 12 Configuration2 Configuration B-5 13 Configuration 2 Configuration B-6 14Configuration 2 Configuration B-7 15 Configuration 3 Configuration B-116 Configuration 3 Configuration B-2 17 Configuration 3 ConfigurationB-3 18 Configuration 3 Configuration B-4 19 Configuration 3Configuration B-5 20 Configuration 3 Configuration B-6 21 Configuration3 Configuration B-7 22 Configuration 4 Configuration B-1 23Configuration 4 Configuration B-2 24 Configuration 4 Configuration B-325 Configuration 4 Configuration B-4 26 Configuration 4 ConfigurationB-5 27 Configuration 4 Configuration B-6 28 Configuration 4Configuration B-7 29 Configuration 5 Configuration B-1 30 Configuration5 Configuration B-2 31 Configuration 5 Configuration B-3 32Configuration 5 Configuration B-4 33 Configuration 5 Configuration B-534 Configuration 5 Configuration B-6 35 Configuration 5 ConfigurationB-7 36 Configuration 6 Configuration B-1 37 Configuration 6Configuration B-2 38 Configuration 6 Configuration B-3 39 Configuration6 Configuration B-4 40 Configuration 6 Configuration B-5 41Configuration 6 Configuration B-6 42 Configuration 6 Configuration B-743 Configuration 7 Configuration B-1 44 Configuration 7 ConfigurationB-2 45 Configuration 7 Configuration B-3 46 Configuration 7Configuration B-4 47 Configuration 7 Configuration B-5 48 Configuration7 Configuration B-6 49 Configuration 7 Configuration B-7 50Configuration 8 Configuration B-1 51 Configuration 8 Configuration B-252 Configuration 8 Configuration B-3 53 Configuration 8 ConfigurationB-4 54 Configuration 8 Configuration B-5 55 Configuration 8Configuration B-6 56 Configuration 8 Configuration B-7 57 Configuration9 Configuration B-1 58 Configuration 9 Configuration B-2 59Configuration 9 Configuration B-3 60 Configuration 9 Configuration B-461 Configuration 9 Configuration B-5 62 Configuration 9 ConfigurationB-6 63 Configuration 9 Configuration B-7 64 Configuration 10Configuration B-1 65 Configuration 10 Configuration B-2 66 Configuration10 Configuration B-3 67 Configuration 10 Configuration B-4 68Configuration 10 Configuration B-5 69 Configuration 10 Configuration B-670 Configuration 10 Configuration B-7 71 Configuration 11 ConfigurationB-1 72 Configuration 11 Configuration B-2 73 Configuration 11Configuration B-3 74 Configuration 11 Configuration B-4 75 Configuration11 Configuration B-5 76 Configuration 11 Configuration B-6 77Configuration 11 Configuration B-7 78 Configuration 12 Configuration B-179 Configuration 12 Configuration B-2 80 Configuration 12 ConfigurationB-3 81 Configuration 12 Configuration B-4 82 Configuration 12Configuration B-5 83 Configuration 12 Configuration B-6 84 Configuration12 Configuration B-7 85 Configuration 13 Configuration B-1 86Configuration 13 Configuration B-2 87 Configuration 13 Configuration B-388 Configuration 13 Configuration B-4 89 Configuration 13 ConfigurationB-5 90 Configuration 13 Configuration B-6 91 Configuration 13Configuration B-7 92 Configuration 14 Configuration B-1 93 Configuration14 Configuration B-2 94 Configuration 14 Configuration B-3 95Configuration 14 Configuration B-4 96 Configuration 14 Configuration B-597 Configuration 14 Configuration B-6 98 Configuration 14 ConfigurationB-7 99 Configuration 15 Configuration B-1 100 Configuration 15Configuration B-2 101 Configuration 15 Configuration B-3 102Configuration 15 Configuration B-4 103 Configuration 15 ConfigurationB-5 104 Configuration 15 Configuration B-6 105 Configuration 15Configuration B-7 106 Configuration 16 Configuration B-1 107Configuration 16 Configuration B-2 108 Configuration 16 ConfigurationB-3 109 Configuration 16 Configuration B-4 110 Configuration 16Configuration B-5 111 Configuration 16 Configuration B-6 112Configuration 16 Configuration B-7 113 Configuration 17 ConfigurationB-1 114 Configuration 17 Configuration B-2 115 Configuration 17Configuration B-3 116 Configuration 17 Configuration B-4 117Configuration 17 Configuration B-5 118 Configuration 17 ConfigurationB-6 119 Configuration 17 Configuration B-7 120 Configuration 18Configuration B-1 121 Configuration 18 Configuration B-2 122Configuration 18 Configuration B-3 123 Configuration 18 ConfigurationB-4 124 Configuration 18 Configuration B-5 125 Configuration 18Configuration B-6 126 Configuration 18 Configuration B-7 127Configuration 19 Configuration B-1 128 Configuration 19 ConfigurationB-2 129 Configuration 19 Configuration B-3 130 Configuration 19Configuration B-4 131 Configuration 19 Configuration B-5 132Configuration 19 Configuration B-6 133 Configuration 19 ConfigurationB-7

Preferably, the organozinc base is used in the process according to theinvention in a total amount of 0.5 to 5 equivalents, preferably of 0.8to 2 equivalents, further preferably of 1 to 1.5 equivalents and morepreferably of 1.0 to 1.2 equivalents, based on the compound Q-H. Oneadvantage of the process according to the invention in this regard isthat the organometallic base can be used in virtually stoichiometricamounts.

Depending on whether the structural element (NR³R⁴) is present once ortwice in the organozinc base used, intermediate compounds of the formula(IIIa) or of the formula (IIIb) are formed in process step a).

The conversion of the compounds of the formula (IIIa) or (IIIb) tocompounds of the formula (II) in the second process step (step b)) iseffected in the presence of a compound of the formula (I)

in which X, W and Y each have the definitions given above.

During the Negishi cross-coupling, the reaction takes place virtuallyexclusively at position 2, since iodine is the best leaving group on thepyridine skeleton. It then regioselectively affords the correspondingpyridine derivative of the formula (II).

Compounds of the formula (I) can be obtained, for example, bysubstitution of an appropriate precursor compound, i.e. a pyridinederivative with the W and Y radicals, by the X radical. Such asubstitution can be effected, for example, by metallation of theprecursor compound in the presence of zinc bases and subsequent reactionwith elemental halogen. Metallations of this kind with substitutedpyridines, for example, at the 4 position are described in AngewandteChemie 2007 (46), p. 7685ff or Organic Letters 2009 (11), p. 1837ff.

Preferably, the compound of the formula (I) is used in the processaccording to the invention in a total amount of 0.5 to 10.0 equivalents,preferably of 0.8 to 5 equivalents, further preferably of 1 to 2.5equivalents and more preferably of 1.0 to 1.5 equivalents or morepreferably of 1.5 to 2.0 equivalents or more preferably of 1.0 to 2.0equivalents, based on the compound Q-H.

The conversion in process step b) is further effected in the presence ofa catalyst. Preferably, the catalyst is a palladium compound or a nickelcompound. More preferably, the catalyst is a palladium compound. It ismost preferably tetrakis(triphenylphosphine)palladium(0), abbreviated toPd(PPh₃)₄, of the formula (IX).

Typically, in a process according to the invention, 2.5-25 mol % andpreferably 5-20 mol % of catalyst is used.

The inventive conversion of the compounds Q-H to compounds of theformula (IIIa) or (IIIb) and further to compounds of the formula (II) ispreferably effected in the presence of an organic solvent in each case.Useful solvents in principle include all organic solvents which areinert under the reaction conditions employed and in which the compoundsto be converted have adequate solubility. Suitable solvents especiallyinclude: tetrahydrofuran (THF), 1,4-dioxane, diethyl ether, diglyme,methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene, xylenes, mesitylene, ethylene carbonate,propylene carbonate, N,N-dimethylacetamide, N,N-dimethylformamide (DMF),N-methylpyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP),N-butyl-2-pyrrolidone (NBP); N,N′-dimethylpropyleneurea (DMPU),halohydrocarbons and aromatic hydrocarbons, especiallychlorohydrocarbons such as tetrachloroethylene, tetrachloroethane,dichloropropane, methylene chloride, dichlorobutane, chloroform, carbontetrachloride, trichloroethane, trichloroethylene, pentachloroethane,difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene,dichlorobenzene, especially 1,2-dichlorobenzene, chlorotoluene,trichlorobenzene; 4-methoxybenzene, fluorinated aliphatics andaromatics, such as trichlorotrifluoroethane, benzotrifluoride and4-chlorobenzotrifluoride. It is also possible to use solvent mixtures,preferably mixtures of the aforementioned solvents such astetrahydrofuran (THF), 1,4-dioxane, diethyl ether, diglyme, methyltert-butyl ether (MTBE), tert-amyl methyl ether (TAME), 2-methyl-THF,toluene, xylenes, mesitylene, dimethylformamide (DMF).

Preferred solvents are THF, N,N-dimethylformamide (DMF), 1,4-dioxane,diglyme, methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene and 4-methoxybenzene.

Particularly preferred solvents are THF and N,N-dimethylformamide (DMF),very particular preference being given to THF.

The solvent may also be degassed (oxygen-free).

Preference is given to using the same solvent for both process steps a)and b). Alternative configurations of the invention in which differentsolvents are used for process steps a) and b) are likewise possible,however, in which case the solvents are likewise preferably selectedfrom the aforementioned solvents, and the respective solvents specifiedas being preferred, more preferred and most preferred are applicable tothe respective process step a) or b).

The conversion in process step a) is generally conducted at atemperature between 0° C. and 80° C. and with increasing preferencebetween 10° C. and 70° C., between 15° C. and 60° C., between 20° C. and50° C., between 20° C. and 40° C., and most preferably between 20° C.and 35° C., for example at room temperature or 25° C.

The conversion in process step b) is generally conducted at atemperature between 40° C. and 90° C. and with increasing preferencebetween 50° C. and 85° C., between 55° C. and 80° C., between 60° C. and80° C., and most preferably between 65° C. and 75° C., for example at65° C.

The reaction is typically conducted at standard pressure, but can alsobe conducted at elevated or reduced pressure.

The desired compounds of the formula (II) can be isolated, for example,by aqueous workup in the presence of saturated ammonium chloride orsodium thiosulphate solutions and/or subsequent chromatography. Suchprocesses are known to those skilled in the art and also includecrystallization from an organic solvent or solvent mixture.

One example of a particularly preferred embodiment of the processaccording to the invention can be elucidated with reference to thefollowing scheme (II):

In this scheme, A, W and Y have the definitions given above. Thecompound shown in brackets represents the corresponding intermediate ofthe formula IIIa which is converted further to the product, a compoundof the formula (II). Both reactions take place in THF as solvent.“equiv” refers to the amount of equivalents of TMPZnCl.LiCl or compoundof the formula (I) used. Pd(0) represents a palladium compound ascatalyst, preferably in the form of Pd(PPh₃)₄.

The present invention further provides compounds of the structure Q-H inwhich (configuration Q-H-1-1)

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon.

An alternative embodiment is that of compounds of the structure Q-H

in which (configuration Q-H-1-2)

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and    -   A is cyano, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,        (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon.

Preferably, Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ in configuration Q-H-1-1 andconfiguration Q-H-1-2 represent not more than five nitrogen atomsoverall and further preferably not more than four nitrogen atomsoverall.

Preferred (configuration Q-H-2-1 and Q-H-2-2), particularly preferred(configuration Q-H-3-1) and very particularly preferred (configurationQ-H-4-1) definitions of the radicals included in the compounds Q-Hmentioned in the above configurations Q-H-1-1 and Q-H-1-2 are elucidatedhereinafter.

Configuration Q-H-2-1:

-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl.    Configuration Q-H-2-2:-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and-   A is preferably fluoromethyl, difluoromethyl, trifluoromethyl,    fluoroethyl (CH₂CFH₂, CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂,    CHFCFH₂), trifluoroethyl, (CH₂CF₃, CHFCHF₂, CF₂CFH₂),    tetrafluoroethyl (CHFCF₃, CF₂CHF₂), pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl.    Configuration Q-H-3-1:-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    and-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl.    Configuration Q-H-4-1:-   Q is most preferably the structural element Q3 or Q14,-   R⁷ is most preferably methyl, ethyl, n-propyl or isopropyl,    especially methyl, and-   A is most preferably trifluoromethyl.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective ranges ofpreference.

Preference is given in accordance with the invention to those compoundsin which there is a combination of the definitions listed above as beingpreferred.

Particular preference is given in accordance with the invention to thosecompounds in which there is a combination of the definitions listedabove as being more preferred.

Very particular preference is given in accordance with the invention tothose compounds in which there is a combination of the definitionslisted above as being most preferred.

One example of such a very particularly preferred compound is:

-   3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

-   7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

The present invention further provides compounds of the formula (IIIa)

in which

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon, and    -   R² is halogen or —O-pivaloyl.

Preferably, Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ represent not more than fivenitrogen atoms overall and further preferably not more than fournitrogen atoms overall.

Preferred, particularly preferred and very particularly preferreddefinitions of the radicals included in the aforementioned compounds ofthe formula (IIIa) are elucidated hereinafter.

-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl, and-   R² is preferably halogen, especially chlorine, bromine or iodine.-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl, and-   R² is more preferably chlorine.-   Q is most preferably the structural element Q3 or Q14,-   R⁷ is most preferably methyl, ethyl, n-propyl or isopropyl,    especially methyl,-   A is most preferably trifluoromethyl, and-   R² is most preferably chlorine.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective ranges ofpreference.

Preference is given in accordance with the invention to those compoundsin which there is a combination of the definitions listed above as beingpreferred.

Particular preference is given in accordance with the invention to thosecompounds in which there is a combination of the definitions listedabove as being more preferred.

Very particular preference is given in accordance with the invention tothose compounds in which there is a combination of the definitionslisted above as being most preferred.

The compounds of the formula (IIIa) may also be present on their own oras the alkali metal or alkaline earth metal halide complex, preferablyas the lithium chloride complex.

Examples of such very particularly preferred compounds are:

The present invention further provides compounds of the formula (IIIb)Q-Zn-Q  (IIIb)in which

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon.

Preferably, Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ represent not more than fivenitrogen atoms overall and further preferably not more than fournitrogen atoms overall.

Preferred, particularly preferred and very particularly preferreddefinitions of the radicals included in the aforementioned compounds ofthe formula (IIIb) are elucidated hereinafter.

-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl.-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    and-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl.-   Q is most preferably the structural element Q3 or Q14,-   R⁷ is most preferably methyl, ethyl, n-propyl or isopropyl,    especially methyl, and-   A is most preferably trifluoromethyl.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective ranges ofpreference.

Preference is given in accordance with the invention to those compoundsin which there is a combination of the definitions listed above as beingpreferred.

Particular preference is given in accordance with the invention to thosecompounds in which there is a combination of the definitions listedabove as being more preferred.

Very particular preference is given in accordance with the invention tothose compounds in which there is a combination of the definitionslisted above as being most preferred.

The compounds of the formula (IIIb) may also be present on their own oras the alkali metal or alkaline earth metal halide complex, preferablyas the lithium chloride complex.

The present invention further provides compounds of the formula (II)

in which (configuration II-1-1)

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon,

-   W is halogen, and

-   Y is halogen, CO₂R¹ or NO₂, where R¹ is (C₁-C₆)-alkyl or    (C₁-C₆)-haloalkyl.

An alternative embodiment (configuration II-1-2) is that of compounds ofthe formula (II) in which

-   Q is a structural element

-   -   where the symbol # indicates the bond to the rest of the        molecule and    -   Q¹ is N or CR⁶,    -   Q² is N or CR⁶,    -   Q³ is N or C,    -   Q⁴ is O, S, N or NR⁷,    -   Q⁵ is N or C,    -   Q⁶ is N or CH,    -   R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    -   A is hydrogen, cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl        or di-(C₁-C₄)alkylaminosulphonyl,    -   or A is —O—CF₂—O— and, together with Q¹ and the carbon atom to        which it is bonded, forms a five-membered ring where Q¹ is        carbon,

-   W is fluorine or bromine, and

-   Y is halogen, CO₂R¹ or NO₂, where R¹ is (C₁-C₆)-alkyl or    (C₁-C₆)-haloalkyl.

Preferably, Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ in configuration II-1-1 andconfiguration II-1-2 represent not more than five nitrogen atoms overalland further preferably not more than four nitrogen atoms overall.

Preferred (configurations II-2-1 and II-2-2), particularly preferred(configurations II-3-1 and II-3-2) and very particularly preferred(configuration II-4-1) definitions of the radicals included in theaforementioned formula (II) are elucidated hereinafter.

Configuration II-2-1:

-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl,-   W is preferably fluorine or bromine, and-   Y is preferably fluorine, chlorine, bromine, CO₂R¹ or NO₂, where R¹    is (C₁-C₄)-alkyl.    Configuration II-2-2:-   Q is preferably a structural element from the group of Q1 to Q15-   R⁷ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   A is preferably fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphonyl,-   W is preferably fluorine or bromine, and-   Y is preferably fluorine, chlorine, bromine, CO₂R¹ or NO₂, where R¹    is (C₁-C₄)-alkyl.    Configuration II-3-1:-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl,-   W is more preferably fluorine or chlorine, especially fluorine, and-   Y is more preferably chlorine, bromine, CO₂R¹ or NO₂, where R¹ is    (C₁-C₄)-alkyl.    Configuration II-3-2:-   Q is more preferably a structural element from the group of Q2, Q3,    Q10, Q12, Q14 and Q15-   R⁷ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   A is more preferably trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphinyl or    trifluoromethylsulphonyl,-   W is more preferably fluorine, and-   Y is more preferably chlorine, bromine, CO₂R¹ or NO₂, where R¹ is    (C₁-C₄)-alkyl.    Configuration II-4-1:-   Q is most preferably the structural element Q3 or Q14,-   R⁷ is most preferably methyl, ethyl, n-propyl or isopropyl,    especially methyl,-   A is most preferably trifluoromethyl,-   W is most preferably fluorine, and-   Y is most preferably chlorine, bromine, CO₂R¹ or NO₂, where R¹ is    methyl.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective ranges ofpreference.

Preference is given in accordance with the invention to those compoundsin which there is a combination of the definitions listed above as beingpreferred.

Particular preference is given in accordance with the invention to thosecompounds in which there is a combination of the definitions listedabove as being more preferred.

Very particular preference is given in accordance with the invention tothose compounds in which there is a combination of the definitionslisted above as being most preferred.

Examples of such very particularly preferred compounds are:

-   2-(6-Chloro-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

-   2-(6-Bromo-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

-   Methyl    5-fluoro-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-2-yl]pyridine-2-carboxylate

-   2-(3-Fluoro-6-nitropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

-   6-(6-Chloro-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

-   Methyl    5-fluoro-6-[7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]pyridine-2-carboxylate

-   6-(6-Bromo-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

The present invention is elucidated in detail by the examples whichfollow, although the examples should not be interpreted in such a mannerthat they restrict the invention.

Example 1 Synthesis of3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

N3-Methyl-6-(trifluoromethyl)pyridine-3,4-diamine (500 mg, 2.6 mmol),dissolved in formic acid (4 ml, 106 mmol), was heated with microwaves at150° C. for 1 hour. After customary workup by addition of saturatedaqueous ammonium chloride solution, the reaction mixture was extractedwith ethyl acetate, and the combined organic phases were dried overNa₂SO₄ and concentrated in a membrane pump vacuum. After purification bycolumn chromatography (ethyl acetate/cyclohexane),3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (480 mg, 91%) wasobtained as a white solid. HPLC-MS: log P=1.09; Mass (m/z+1): 202.0;1HNMR (D6-DMSO): δ 9.14 (s, 1H), 8.61 (s, 1H), 8.19 (s, 1H), 4.02 (s,3H).

Example 2 Synthesis of2-(6-chloro-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (201 mg, 1.0mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,0.84 ml, 1.1 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, 6-chloro-3-fluoro-2-iodopyridine (515mg, 2 mmol in 4 ml THF) and tetrakis(triphenylphosphine)palladium(0)(115 mg, 0.1 mmol) were added at 25° C. and the solution was stirred at65° C. for a further 3 hours. After customary workup by addition ofsaturated aqueous ammonium chloride solution, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),2-(6-chloro-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(177 mg, 52%) was obtained as a white solid. HPLC-MS: log P=2.38; Mass(m/z): 331.0; 1HNMR (D6-DMSO): δ 9.29 (s, 1H), 8.32 (s, 1H), 8.19 (t,1H), 7.91 (dd, 1H), 4.14 (s, 3H).

Example 3 Synthesis of methyl5-fluoro-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylate

To 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (201 mg, 1.0mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,0.84 ml, 1.1 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, methyl5-fluoro-6-iodopyridine-2-carboxylate (562 mg, 2 mmol in 4 ml THF) andtetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) were addedat 25° C. and the solution was stirred at 65° C. for a further 3 hours.After customary workup by addition of saturated aqueous ammoniumchloride solution, the reaction mixture was extracted with ethylacetate, and the combined organic phases were dried over Na₂SO₄ andconcentrated in a membrane pump vacuum. After purification by columnchromatography (ethyl acetate/cyclohexane), methyl5-fluoro-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylate(160 mg, 45%) was obtained as a white solid. HPLC-MS: log P==2.03; Mass(m/z+1): 355.1; 1HNMR (D6-DMSO): 9.30 (s, 1H), 8.38 (dd, 1H), 8.34 (s,1H), 8.24 (dd, 1H), 4.19 (s, 3H), 3.93 (s, 3H).

Example 4 Synthesis of2-(6-bromo-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (100 mg, 0.5mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,0.52 ml, 0.55 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, 6-bromo-3-fluoro-2-iodopyridine (301mg, 1 mmol in 2 ml THF) and tetrakis(triphenylphosphine)palladium(0) (58mg, 0.05 mmol) were added at 25° C. and the solution was stirred at 65°C. for a further 3 hours. After customary workup by addition ofsaturated aqueous ammonium chloride solution, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),2-(6-bromo-3-fluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(101 mg, 54%) was obtained as a white solid. HPLC-MS: log P=2.51; Mass(m/z+1): 376.9; 1HNMR (D6-DMSO): δ 9.29 (s, 1H), 8.33 (s, 1H), 8.05 (m,2H), 4.13 (s, 3H).

Example 5 Synthesis of7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

N3-Methyl-6-(trifluoromethyl)pyridazine-3,4-diamine (192 mg, 1.0 mmol),dissolved in formic acid (0.4 ml, 106 mmol), was heated with microwavesat 150° C. for 2 hours. After customary workup by addition of saturatedaqueous ammonium chloride solution, the reaction mixture was extractedwith ethyl acetate, and the combined organic phases were dried overNa₂SO₄ and concentrated in a membrane pump vacuum. After purification bycolumn chromatography (ethyl acetate/cyclohexane),7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine (149 mg, 74%)was obtained as a white solid. HPLC-MS: log P=0.95; Mass (m/z+1): 203.1;1HNMR (D6-DMSO): δ 8.97 (s, 1H), 8.62 (s, 1H), 4.08 (s, 3H).

Example 6 Synthesis of6-(6-chloro-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

To 7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine (202 mg, 1.0mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,0.84 ml, 1.1 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, 6-chloro-3-fluoro-2-iodopyridine (515mg, 2 mmol in 4 ml THF) and tetrakis(triphenylphosphine)palladium(0)(115 mg, 0.1 mmol) were added at 25° C. and the solution was stirred at65° C. for a further 3 hours. After customary workup by addition ofsaturated aqueous ammonium chloride solution, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),6-(6-chloro-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine(125 mg, 38%) was obtained as a white solid. HPLC-MS: log P=2.46; Mass(m/z): 332.0; 1HNMR (D6-DMSO): δ 8.77 (s, 1H), 8.23 (t, 1H), 7.98 (dd,1H), 4.25 (s, 3H).

Example 7 Synthesis of methyl5-fluoro-6-[7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]pyridine-2-carboxylate

To 7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine (202 mg, 1.0mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,0.84 ml, 1.1 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, methyl5-fluoro-6-iodopyridine-2-carboxylate (562 mg, 2 mmol in 4 ml THF) andtetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) were addedat 25° C. and the solution was stirred at 65° C. for a further 3 hours.After customary workup by addition of saturated aqueous ammoniumchloride solution, the reaction mixture was extracted with ethylacetate, and the combined organic phases were dried over Na₂SO₄ andconcentrated in a membrane pump vacuum. After purification by columnchromatography (ethyl acetate/cyclohexane), methyl5-fluoro-6-[7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]pyridine-2-carboxylate(208 mg, 59%) was obtained as a white solid. HPLC-MS: log P==2.09; Mass(m/z+1): 356.0; 1HNMR (D6-DMSO): 8.78 (s, 1H), 8.43 (dd, 1H), 8.28 (t,1H), 4.32 (s, 3H), 3.96 (s, 3H).

Example 8 Synthesis of6-(6-bromo-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine

To 7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine (340 mg, 1.7mmol), dissolved in THF (2 ml), was added TMPZnCl.LiCl (1.31 M in THF,1.41 ml, 1.85 mmol) at 25° C. under argon; this reaction solution wasstirred for 10 min. Subsequently, 6-bromo-3-fluoro-2-iodopyridine (1.016g, 3.36 mmol in 4 ml THF) and tetrakis(triphenylphosphine)palladium(0)(195 mg, 0.16 mmol) were added at 25° C. and the solution was stirred at65° C. for a further 3 hours. After customary workup by addition ofsaturated aqueous ammonium chloride solution, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),6-(6-bromo-3-fluoropyridin-2-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine(408 mg, 62%) was obtained as a white solid. HPLC-MS: log P=2.58; Mass(m/z+1): 375.9; 1HNMR (D6-DMSO): δ 8.77 (s, 1H), 8.10 (m, 2H), 4.25 (s,3H)

The invention claimed is:
 1. Process for preparing compound of formula(II)

in which Q is a structural element

where the symbol # indicates the bond to the rest of the molecule and Q¹is N or CR⁶, Q² is N or CR⁶, Q³ is N or C, Q⁴ is O, S, N or NR⁷, Q⁵ is Nor C, Q⁶ is N or CH, R⁶ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, R⁷ is (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and A is hydrogen, cyano, halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylsulphonyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,(C₁-C₄)alkylaminosulphonyl or di-(C₁-C₄)alkylaminosulphonyl, or A is—O—CF₂—O— and, together with Q¹ and the carbon atom to which it isbonded, forms a five-membered ring where Q¹ is carbon, W is halogen, andY is halogen, CO₂R¹ or NO₂, where R¹ is (C₁-C₆)-alkyl or(C₁-C₆)-haloalkyl, wherein, first a), a compound Q-H in which Q is asdefined above is reacted with an organozinc base of the structure(NR³R⁴)—Zn—R² or (NR³R⁴)₂—Zn in which R² is halogen or —O-pivaloyl andR³ and R⁴ together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂— group,where each of these groups may optionally be substituted by 1, 2, 3 or 4R⁵ radicals and R⁵ is selected from the group consisting of methyl,ethyl, n-propyl and i-propyl, to give a compound of formula (IIIa) orformula (IIIb)

in which Q and R² each have the definitions given above, and saidcompound of formula (IIIa) or (IIIb) is reacted in b) with a compound offormula (I)

in which X is halogen and W and Y each have the definitions given above,in the presence of a catalyst, to give the compound of formula (II). 2.Process according to claim 1, wherein Q is a structural element from thegroup of Q1 to Q15

R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, A is fluorine, chlorine, bromine,fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl,(CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, W is fluorine, chlorine or bromine, R² ishalogen, X is halogen, and Y is fluorine, chlorine, bromine, CO₂R orNO₂, where R¹ is (C₁-C₄)-alkyl.
 3. Process according to claim 1, whereinQ is a structural element from the group of Q2, Q3, Q10, Q12, Q14 andQ15 R⁷ is (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl, A istrifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃), difluoroethyl (CF₂CH₃,CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃, CHFCHF₂, CF₂CFH₂),tetrafluoroethyl (CHFCF₃, CF₂CHF₂), pentafluoroethyl,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, W is fluorine or chlorine, R² is chlorine, Xis bromine or iodine, and Y is chlorine, bromine, CO₂R¹ or NO₂, where R¹is (C₁-C₄)-alkyl.
 4. Process according to claim 1, wherein Q is thestructural element Q3 or Q14 R⁷ is methyl, ethyl, n-propyl or isopropyl,A is trifluoromethyl, W is fluorine, R² is chlorine, X is iodine, and Yis chlorine, bromine, CO₂R or NO₂, where R¹ is methyl.
 5. Processaccording to claim 1, wherein R³ and R⁴ together form a —(CH₂)₅— groupsubstituted by 4 methyl groups.
 6. Process according to claim 1, whereinthe organozinc base is a compound of formula (V)(TMP)_(x) ZnCl_(2-x)  (V) in which x is the number 1 or
 2. 7. Processaccording to claim 1, wherein the organozinc base is present inconjunction with an alkali metal halide or alkaline earth metal halide.8. Process according to claim 1, wherein the organozinc base is used ina total amount of 0.5 to 5 equivalents, based on the compound Q-H. 9.Process according to claim 1, wherein the compound of formula (I) isused in a total amount of 0.5 to 10.0 equivalents, based on the compoundQ-H.
 10. Process according to claim 1, wherein the catalyst is apalladium compound.
 11. Process according to claim 1, wherein thecatalyst is tetrakis(triphenylphosphine)palladium(0).
 12. Processaccording to claim 1, that is conducted in the presence of a solventselected from the group consisting of tetrahydrofuran (THF),1,4-dioxane, diethyl ether, diglyme, methyl tert-butyl ether (MTBE),tert-amyl methyl ether (TAME), 2-methyl-THF, toluene, xylenes,mesitylene, ethylene carbonate, propylene carbonate,N,N-dimethylacetamide, N,N-dimethylformamide (DMF), N-methylpyrrolidone(NMP), N-ethyl-2-pyrrolidone (NEP), N-butyl-2-pyrrolidone (NBP);N,N′-dimethylpropyleneurea (DMPU), halohydrocarbon, aromatichydrocarbon, chlorohydrocarbon, tetrachloroethylene, tetrachloroethane,dichloropropane, methylene chloride, dichlorobutane, chloroform, carbontetrachloride, trichloroethane, trichloroethylene, pentachloroethane,difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene,dichlorobenzene, 1,2-dichlorobenzene, chlorotoluene, trichlorobenzene;4-methoxybenzene, fluorinated aliphatic, fluorinated aromatic,trichlorotrifluoroethane, benzotrifluoride and 4-chlorobenzotrifluoride,or a mixture of at least two of these solvents with one another. 13.Process according to claim 12, wherein the solvent is THF orN,N-dimethylformamide (DMF).
 14. Process according to claim 1, whereina) is conducted at a temperature between 0° C. and 80° C.
 15. Processaccording to claim 1, wherein b) is conducted at a temperature between40° C. and 90° C.
 16. Compound of structure Q-H in which Q is astructural element from the group of Q1 to Q15

R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or(C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, A is fluorine, chlorine, bromine,fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl,(CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl,


17. Compound of formula (IIIa)

in which Q is a structural element from the group of Q1 to Q15

R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, A is fluorine, chlorine, bromine,fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl,(CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, and R² is halogen.
 18. Compound of formula(IIIb)Q-Zn-Q   (IIIb) in which Q is a structural element from the group of Q1to Q15

R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, and A is fluorine, chlorine,bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl(CH₂CFH₂, CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂),trifluoroethyl, (CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃,CF₂CHF₂), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl.
 19. Compound of formula (II)

in which Q is a structural element from the group of Q1 to Q15

R⁷ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, A is fluorine, chlorine, bromine,fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl,(CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, W is fluorine or bromine, and Y is fluorine,chlorine, bromine, CO₂R or NO₂, where R is (C₁-C₄)-alkyl.